Hydrazine hydrate (1:1) → 2'-Fluoro-4-hydroxy-5'-methoxy-[1,1'-biphenyl]-2-carbohydrazide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:17]([O:19]CC)=O)=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1.O.[NH2:23][NH2:24]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:17]([NH:23][NH2:24])=[O:19])=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1Participants
4
Conditions
- Temperature
- 95 °C
Procedure
To a solution of ethyl 2′-fluoro-4-hydroxy-5′-methoxy-[1,1′-biphenyl]-2-carboxylate (1.37 g) in ethanol (15 mL) was added hydrazine monohydrate (4.47 mL), and the mixture was stirred at 95° C. for 46 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane and then methanol/ethyl acetate) to give the title compound (1.05 g) as a white amorphous solid.